Italy: Southern Tuscany & Giglio Island

Your vacation is about to begin! Spend your first night aloft and arrive ready for an unforgettable trip.

A VBT representative will greet you at Rome Airport to start your adventure off right. A complimentary car service will then whisk you to your conveniently located hotel in Orvieto.

The rest of the day is free to explore this remarkable, historic city. Perched atop a dramatic volcanic bluff in the Paglia River Valley, Orvieto boasts centuries of history and architecture—from medieval towers and palaces to noble houses and ancient churches. Originally an important Etruscan center, Orvieto flourished under Roman rule as a hub for ceramic production. After enduring centuries of invasion, it emerged as a free state in the 11th and 12th centuries. In 1354, it became part of the Church Estate, then briefly fell under Napoleonic rule before joining the Kingdom of Italy in 1860. Highlights include Orvieto’s impressive Gothic cathedral, featuring a striking façade of mosaics, stained glass, and sculpture, and the Archaeological Museum, home to an exceptional collection of Etruscan artifacts.

This evening, relax at one of the city’s many restaurants and enjoy a taste of the region’s renowned cuisine.

After an included breakfast, meet your VBT representative at the hotel in Orvieto at 10:00 a.m. Transportation by motorcoach (approximately two hours) will be provided to Antica Fattoria La Parrina. Please note that you will walk approximately half a mile from the hotel to the motorcoach, as large vehicles are not permitted to circulate in the old town. You’ll arrive at La Parrina at approximately 1:00 p.m., where you’ll be introduced to the region’s farm-to-table cuisine with an included lunch featuring fresh vegetables and farm-produced cheeses.

Your Tuscany bike tour officially begins at Antica Fattoria La Parrina, a welcoming four-star agriturismo resort featured in Condé Nast Traveler. Surrounded by beautiful countryside, the estate produces its own wine, cheese, yogurt, vegetables, olive oil, balsamic vinegar, and flowers. It also offers organic pasta, jams, sauces, and natural cosmetics—all made with healthy, locally sourced ingredients. In the afternoon, you’ll join your trip leaders for a safety and bike-fitting session, followed by a short warm-up ride on quiet country roads through the estate.

Later, gather on the terrace for a welcome cocktail reception. Dinner will be served at the hotel.

Today's Ride Choices

Afternoon: Warm-Up Ride — 17 km (11 miles)

What to Expect:

An easy loop ride through the countryside, passing La Parrina’s orchards, local farms, and into the small village of Albinia. The route includes a short stretch on an unpaved but well-maintained track; the rest of the ride follows quiet, paved roads.

Cumulative Distance Range: 17 km (11 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, you’ll leave La Parrina and cycle to the coast and the hilltop village of Talamone, where many Greek legends are tied to its ancient past. During the morning ride, there will be time for a refreshing swim in the glittering blue sea. Overlooking the Mediterranean, Talamone is nestled in the rolling countryside of the Maremma—one of central Italy’s least-developed and most scenic regions. Its skyline is marked by a striking medieval Sienese castle. Once located on nearby Talamonaccio Hill, the original settlement served as an ancient Etruscan port. Today, Talamone lies within a World Wildlife Fund nature reserve known as Parco Regionale della Maremma (Maremma Park), home to a remarkable variety of protected flora and fauna. Lunch is a delicious picnic prepared by your trip leaders.

In the afternoon, cycle back to your hotel, where you can unwind by the beautiful pool or enjoy a walk along mapped trails that weave through the estate. If you prefer, opt for horseback riding in the surrounding countryside, which is known for its native Maremma horse breed. Your trip leaders can help facilitate this activity, but advance reservations are required.

Before dinner, stop by Parrina’s large organic shop to explore its award-winning cheeses, olive oil, wines, and other locally produced specialties. Then head to the kitchen and join your hosts on the terrace for a hands-on cooking class, where you’ll learn to prepare cantucci—classic Tuscan almond cookies traditionally served with sweet Vin Santo wine. Dinner will be served at the hotel.

Today's Ride Choices

Morning: Parrina to Talamone — 31 km (19 miles)

Afternoon: Talamone to Parrina — 25 km (16 miles) OR Talamone to Parrina PLUS — 37 km (23 miles)

What to Expect:

Ride along country roads through a classic Tuscan landscape. After the initial 0.8 miles on unpaved terrain, the remainder of the route is entirely on paved roads with very limited car traffic. The ride includes a couple of easy, short hills. If you prefer to skip the afternoon ride, the support vehicle will be available to shuttle you back to the hotel.

Cumulative Distance Range: 25 — 68 km (16 — 42 miles)

Included Meals: Breakfast, Lunch, Dinner

This morning, ride through the countryside toward the coast and Ansedonia, passing elegant villas and gardens while enjoying splendid views of the sea and an old watchtower that once defended this coastline. Along the way, enjoy a picnic lunch at Il Ponte, a typical Maremma family-run winery. The name Il Ponte—meaning both “bridge” and “long weekend” in Italian—reflects the owners’ desire to transform what was once a second home into a place to reconnect as a family and savor life’s special moments, especially during holiday breaks. Our host, Marta, will present the estate’s wine selection and offer a tasting. From the terrace, you’ll take in sweeping views of the sea, the hilltop town of Capalbio, and the surrounding countryside.

In the afternoon, cycle through a thick pine forest, then roll along the edge of a sandy beach—one of the most scenic stretches of the week. If you wish, pause for a refreshing swim.

Later, continue to the Old Town of Orbetello, following a cycling path built across the lagoon. Explore the lush byway around the water, then meet your trip leaders and follow them to a favorite local gelato spot. A short shuttle will return you to your hotel.

This evening, shuttle back to Orbetello for a stroll and some shopping before enjoying dinner on your own. If you prefer, you may remain at the hotel and dine there instead.

Today's Ride Choices

Morning: Parrina to Il Ponte Winery — 33 km (20.5 miles)

Afternoon: Il Ponte Winery to Orbetello — 29 km (18 miles) OR Il Ponte Winery to Orbetello and WWF reserve — 34 km (21 miles)

What to Expect:

This morning’s route is easy, taking you along quiet, paved roads surrounded by vineyards and fields of sunflowers or wheat. A panoramic stretch through the hills near Capalbio leads to our lunch stop. In the afternoon, the ride is mostly flat, except for a short but steep climb to Ansedonia, which is followed by a 5-mile stretch through a nature reserve near the sea, where the terrain is packed and unpaved. A flat, well-paved bike path then follows a shallow lagoon, guiding you to our final destination in Orbetello. If you prefer to skip the climb to Ansedonia, the support vehicle is available. Today may also offer an additional independent ride for experienced cyclists—please ask your trip leaders for details.

Cumulative Distance Range: 29 — 67 km (18 — 41.5 miles)

Included Meals: Breakfast, Lunch

Today, take a break from pedaling to enjoy the tranquility of Giglio Island. Your morning begins with a warm farewell to your hosts at La Parrina, followed by a transfer to the bustling harbor and charming village of Porto Santo Stefano. From this port town, board a ferry to Giglio Island, arriving in the colorful village of Giglio Porto. Accompanied by a local guide, you’ll shuttle up to the walled hilltop town of Giglio Castello to explore the imposing Rocca Pisana fortress. As the island’s oldest inhabited center, Giglio Castello still exudes a strong medieval atmosphere.

Next, continue westward to Campese Beach for an informal lunch at a local seaside restaurant. You’ll have free time to swim or relax on the beach. If you prefer, opt for a scenic hike along the Faraglione cliffs, where you’ll learn about the 700 species of wildflowers and plants that thrive in this remote corner of Tuscany. On your return to Giglio Porto, enjoy a stop for gelato before ferrying back to the mainland.

This evening, arrive at Fattoria di Magliano, a small country resort and your home for the next three nights. Unwind by the pool or soak in the sunset from the landscaped gardens. Dinner will be served at the hotel.

What to Expect:

Non-biking day: Short hike on Giglio Island or relax at beach, guided tour of castle and along the sea on the cliffs.

Included Meals: Breakfast, Dinner

After a leisurely breakfast, set off along quiet country roads, passing fields of poppies, sunflowers, and vineyards that gently slope down to the sea. Ride the scenic wine roads south of Scansano, renowned for producing the bold red Morellino wine. Stop at the Magliano olive oil shop and former mill for an engaging olive oil talk and tasting. Continue cycling through Magliano and enjoy an included lunch on the town’s medieval piazza. In the Middle Ages, this walled city served as the winter residence of the Aldobrandeschi court, and sections of its 14th-century walls remain intact to this day.

From Magliano, those who wish to experience more of Tuscany’s rolling hills by bike may opt for a gentle but steady climb to the charming villages of Pereta and Scansano.

This evening, take a short shuttle into town and choose a restaurant—or perhaps a pizzeria—for dinner on your own.

Today's Ride Choices

Morning: Fattoria to Magliano — 27 km (17 miles)

Afternoon: Magliano to Fattoria — 5 km (3 miles) OR Magliano to Scansano and Fattoria — 36 km (22 miles)

What to Expect:

Today’s ride follows rolling terrain as you cycle toward the walled city of Magliano, where you’ll stop for lunch. In the afternoon, you may choose a short ride back to the hotel or opt for a longer, hillier route via Scansano. While the shorter route covers only a few miles, it includes a very challenging climb—which you can bypass with a five-minute shuttle. The longer loop features a steady, moderate ascent and rewards you with sweeping views of the Tuscan countryside.

Cumulative Distance Range: 27 — 63 km (17 — 39 miles)

Included Meals: Breakfast, Lunch

After breakfast, cycle to the medieval town of Capalbio. Dating back to the 11th century, this historic hilltop town is enclosed by impressive stone walls. Stroll along the ancient ramparts and take in panoramic views of the surrounding countryside. Enter the Old Town through one of two gates—the Sienese Gate or the Porticina—and visit the Romanesque Church of Saint Nicholas, notable for its dramatic bell tower featuring two rows of mullioned windows from the 12th century. Enjoy time to explore Capalbio’s winding cobblestone streets, medieval churches, and charming shops. Afterward, complete your rewarding ride back to the hotel—or, if you prefer, opt for a shuttle.

This afternoon, relax at the hotel or take a dip in the pool before sampling the estate’s wines during an included tasting. Fattoria di Magliano is one of the region’s most acclaimed producers of Tuscan wine, recognized for helping shape the evolution of modern Italian winemaking.

This evening, enjoy an aperitivo as the sun sets behind the Tuscan hills one final time, then gather with fellow travelers for a festive farewell dinner at your agriturismo.

Today's Ride Choices

Morning: Fattoria to Capalbio — 29 km (18 miles)

Afternoon: Capalbio to shuttle point — 20 km (12 miles)

What to Expect:

After an exhilarating downhill from our hotel on a paved road with little car traffic, you cycle along a slightly rolling road before a gradual uphill to Capalbio. Loop back on a different route, mostly downhill on a very scenic road. You may take the support vehicle back to the hotel from La Sgrilla or continue on a rolling road with little traffic.

Today may offer an additional independent ride for experienced cyclists. Ask your trip leader for details.

Cumulative Distance Range: 20 — 49 km (12 — 30 miles)

Included Meals: Breakfast, Dinner

After an included breakfast, complimentary transportation is provided by private motorcoach (approximately three hours) to our centrally located Rome hotel for your final overnight stay. You’ll arrive at approximately 11:30 a.m., with the rest of the day free to shop, explore, or relax at one of the city’s many outdoor cafés.

Upon arrival, a VBT Rome representative will be available to answer your questions. Optional walking tours of Rome will be offered—please refer to your VBT city information for details.

Included Meals: Breakfast

After an included breakfast this morning, complimentary transportation to Rome Airport will be provided (an approximately 40- to 60-minute drive, depending on traffic) for your departing flight.

Included Meals: Breakfast

Meet your VBT trip leaders inside the Orbetello-Monte Argentario train station at 2:15 p.m. They will be wearing VBT staff apparel for easy identification. Lunch is included at La Parrina, and the hotel will set aside a plate of fresh vegetables and farm-produced cheeses for you to enjoy upon arrival.

Alternatively, you may meet your group at our Pre-Tour hotel in Orvieto at 10:00 a.m. From there, you will travel by motorcoach (approximately two hours) to Antica Fattoria La Parrina.

Your Tuscany bike tour officially begins at Antica Fattoria La Parrina, a welcoming four-star agriturismo resort featured in Condé Nast Traveler. Surrounded by beautiful countryside, the estate produces its own wine, cheese, yogurt, vegetables, olive oil, balsamic vinegar, and flowers. It also offers organic pasta, jams, sauces, and natural cosmetics—all made with healthy, locally sourced ingredients. In the afternoon, you’ll join your trip leaders for a safety and bike-fitting session, followed by a short warm-up ride on quiet country roads through the estate.

Later, gather on the terrace for a welcome cocktail reception. Dinner will be served at the hotel.

Today's Ride Choices

Afternoon: Warm-Up Ride — 17 km (11 miles)

What to Expect:

An easy loop ride through the countryside, passing La Parrina’s orchards, local farms, and into the small village of Albinia. The route includes a short stretch on an unpaved but well-maintained track; the rest of the ride follows quiet, paved roads.

Cumulative Distance Range: 17 km (11 miles)

Included Meals: Lunch, Dinner

After breakfast, you’ll leave La Parrina and cycle to the coast and the hilltop village of Talamone, where many Greek legends are tied to its ancient past. During the morning ride, there will be time for a refreshing swim in the glittering blue sea. Overlooking the Mediterranean, Talamone is nestled in the rolling countryside of the Maremma—one of central Italy’s least-developed and most scenic regions. Its skyline is marked by a striking medieval Sienese castle. Once located on nearby Talamonaccio Hill, the original settlement served as an ancient Etruscan port. Today, Talamone lies within a World Wildlife Fund nature reserve known as Parco Regionale della Maremma (Maremma Park), home to a remarkable variety of protected flora and fauna. Lunch is a delicious picnic prepared by your trip leaders.

In the afternoon, cycle back to your hotel, where you can unwind by the beautiful pool or enjoy a walk along mapped trails that weave through the estate. If you prefer, opt for horseback riding in the surrounding countryside, which is known for its native Maremma horse breed. Your trip leaders can help facilitate this activity, but advance reservations are required.

Before dinner, stop by Parrina’s large organic shop to explore its award-winning cheeses, olive oil, wines, and other locally produced specialties. Then head to the kitchen and join your hosts on the terrace for a hands-on cooking class, where you’ll learn to prepare cantucci—classic Tuscan almond cookies traditionally served with sweet Vin Santo wine. Dinner will be served at the hotel.

Today's Ride Choices

Morning: Parrina to Talamone — 31 km (19 miles)

Afternoon: Talamone to Parrina — 25 km (16 miles) OR Talamone to Parrina PLUS — 37 km (23 miles)

What to Expect:

Ride along country roads through a classic Tuscan landscape. After the initial 0.8 miles on unpaved terrain, the remainder of the route is entirely on paved roads with very limited car traffic. The ride includes a couple of easy, short hills. If you prefer to skip the afternoon ride, the support vehicle will be available to shuttle you back to the hotel.

Cumulative Distance Range: 25 — 68 km (16 — 42 miles)

Included Meals: Breakfast, Lunch, Dinner

This morning, ride through the countryside toward the coast and Ansedonia, passing elegant villas and gardens while enjoying splendid views of the sea and an old watchtower that once defended this coastline. Along the way, enjoy a picnic lunch at Il Ponte, a typical Maremma family-run winery. The name Il Ponte—meaning both “bridge” and “long weekend” in Italian—reflects the owners’ desire to transform what was once a second home into a place to reconnect as a family and savor life’s special moments, especially during holiday breaks. Our host, Marta, will present the estate’s wine selection and offer a tasting. From the terrace, you’ll take in sweeping views of the sea, the hilltop town of Capalbio, and the surrounding countryside.

In the afternoon, cycle through a thick pine forest, then roll along the edge of a sandy beach—one of the most scenic stretches of the week. If you wish, pause for a refreshing swim.

Later, continue to the Old Town of Orbetello, following a cycling path built across the lagoon. Explore the lush byway around the water, then meet your trip leaders and follow them to a favorite local gelato spot. A short shuttle will return you to your hotel.

This evening, shuttle back to Orbetello for a stroll and some shopping before enjoying dinner on your own. If you prefer, you may remain at the hotel and dine there instead.

Today's Ride Choices

Morning: Parrina to Il Ponte Winery — 33 km (20.5 miles)

Afternoon: Il Ponte Winery to Orbetello — 29 km (18 miles) OR Il Ponte Winery to Orbetello and WWF reserve — 34 km (21 miles)

What to Expect:

This morning’s route is easy, taking you along quiet, paved roads surrounded by vineyards and fields of sunflowers or wheat. A panoramic stretch through the hills near Capalbio leads to our lunch stop. In the afternoon, the ride is mostly flat, except for a short but steep climb to Ansedonia, which is followed by a 5-mile stretch through a nature reserve near the sea, where the terrain is packed and unpaved. A flat, well-paved bike path then follows a shallow lagoon, guiding you to our final destination in Orbetello. If you prefer to skip the climb to Ansedonia, the support vehicle is available. Today may also offer an additional independent ride for experienced cyclists—please ask your trip leaders for details.

Cumulative Distance Range: 29 — 67 km (18 — 41.5 miles)

Included Meals: Breakfast, Lunch

Today, take a break from pedaling to enjoy the tranquility of Giglio Island. Your morning begins with a warm farewell to your hosts at La Parrina, followed by a transfer to the bustling harbor and charming village of Porto Santo Stefano. From this port town, board a ferry to Giglio Island, arriving in the colorful village of Giglio Porto. Accompanied by a local guide, you’ll shuttle up to the walled hilltop town of Giglio Castello to explore the imposing Rocca Pisana fortress. As the island’s oldest inhabited center, Giglio Castello still exudes a strong medieval atmosphere.

Next, continue westward to Campese Beach for an informal lunch at a local seaside restaurant. You’ll have free time to swim or relax on the beach. If you prefer, opt for a scenic hike along the Faraglione cliffs, where you’ll learn about the 700 species of wildflowers and plants that thrive in this remote corner of Tuscany. On your return to Giglio Porto, enjoy a stop for gelato before ferrying back to the mainland.

This evening, arrive at Fattoria di Magliano, a small country resort and your home for the next three nights. Unwind by the pool or soak in the sunset from the landscaped gardens. Dinner will be served at the hotel.

What to Expect:

Non-biking day: Short hike on Giglio Island or relax at beach, guided tour of castle and along the sea on the cliffs.

Included Meals: Breakfast, Dinner

After a leisurely breakfast, set off along quiet country roads, passing fields of poppies, sunflowers, and vineyards that gently slope down to the sea. Ride the scenic wine roads south of Scansano, renowned for producing the bold red Morellino wine. Stop at the Magliano olive oil shop and former mill for an engaging olive oil talk and tasting. Continue cycling through Magliano and enjoy an included lunch on the town’s medieval piazza. In the Middle Ages, this walled city served as the winter residence of the Aldobrandeschi court, and sections of its 14th-century walls remain intact to this day.

From Magliano, those who wish to experience more of Tuscany’s rolling hills by bike may opt for a gentle but steady climb to the charming villages of Pereta and Scansano.

This evening, take a short shuttle into town and choose a restaurant—or perhaps a pizzeria—for dinner on your own.

Today's Ride Choices

Morning: Fattoria to Magliano — 27 km (17 miles)

Afternoon: Magliano to Fattoria — 5 km (3 miles) OR Magliano to Scansano and Fattoria — 36 km (22 miles)

What to Expect:

Today’s ride follows rolling terrain as you cycle toward the walled city of Magliano, where you’ll stop for lunch. In the afternoon, you may choose a short ride back to the hotel or opt for a longer, hillier route via Scansano. While the shorter route covers only a few miles, it includes a very challenging climb—which you can bypass with a five-minute shuttle. The longer loop features a steady, moderate ascent and rewards you with sweeping views of the Tuscan countryside.

Cumulative Distance Range: 27 — 63 km (17 — 39 miles)

Included Meals: Breakfast, Lunch

After breakfast, cycle to the medieval town of Capalbio. Dating back to the 11th century, this historic hilltop town is enclosed by impressive stone walls. Stroll along the ancient ramparts and take in panoramic views of the surrounding countryside. Enter the Old Town through one of two gates—the Sienese Gate or the Porticina—and visit the Romanesque Church of Saint Nicholas, notable for its dramatic bell tower featuring two rows of mullioned windows from the 12th century. Enjoy time to explore Capalbio’s winding cobblestone streets, medieval churches, and charming shops. Afterward, complete your rewarding ride back to the hotel—or, if you prefer, opt for a shuttle.

This afternoon, relax at the hotel or take a dip in the pool before sampling the estate’s wines during an included tasting. Fattoria di Magliano is one of the region’s most acclaimed producers of Tuscan wine, recognized for helping shape the evolution of modern Italian winemaking.

This evening, enjoy an aperitivo as the sun sets behind the Tuscan hills one final time, then gather with fellow travelers for a festive farewell dinner at your agriturismo.

Today's Ride Choices

Morning: Fattoria to Capalbio — 29 km (18 miles)

Afternoon: Capalbio to shuttle point — 20 km (12 miles)

What to Expect:

After an exhilarating downhill from our hotel on a paved road with little car traffic, you cycle along a slightly rolling road before a gradual uphill to Capalbio. Loop back on a different route, mostly downhill on a very scenic road. You may take the support vehicle back to the hotel from La Sgrilla or continue on a rolling road with little traffic.

Today may offer an additional independent ride for experienced cyclists. Ask your trip leader for details.

Cumulative Distance Range: 20 — 49 km (12 — 30 miles)

Included Meals: Breakfast, Dinner

After an included breakfast, complimentary transportation will be provided by private motorcoach to the Orbetello-Monte Argentario train station, arriving at approximately 9:30 a.m. If you prefer, you are welcome to remain on the coach and continue to our Rome Post-Tour hotel to begin your own travel plans from there.

Included Meals: Breakfast